2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 69827563, compound

HRID 1839241Notes

Reaction equation

HRID 1839241 reaction equation
[CH:1]([NH:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@H:14]1[C@@H:18]2[O:19][C:20]([CH3:23])([CH3:22])[O:21][C@@H:17]2[C@@H:16]([C:24]([OH:26])=[O:25])[O:15]1)([CH3:3])[CH3:2].[CH2:27](OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>CO>[CH3:27][O:25][C:24]([C@@H:16]1[C@@H:17]2[C@@H:18]([O:19][C:20]([CH3:22])([CH3:23])[O:21]2)[C@H:14]([N:9]2[CH:8]=[N:7][C:6]3[C:10]2=[N:11][CH:12]=[N:13][C:5]=3[NH:4][CH:1]([CH3:3])[CH3:2])[O:15]1)=[O:26]

Participants

4

Reactant 2

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 69827790HCID 69827790, compound

Product 1

HCID 69827563HCID 69827563, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (3aS,4S,6R,6aR)-6-(6-isopropylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (4.82 g) and 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ, 3.36 g) in methanol (150 ml) was heated under reflux for 60 h. After cooling to room temperature, the solution was concentrated in vacuo and the resulting residue partitioned between ethyl acetate (100 ml) and citric acid solution (0.5M, 75 ml). The aqueous layer was extracted with ethyl acetate (4×25 ml) and the combined organic extracts were washed with water (50 ml) and brine (75 ml), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel, eluting with ethyl acetate: cyclohexane (1:1) to afford the title compound as a white solid (3.76 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 60 h
  3. concentrationthe solution was concentrated in vacuo
  4. customthe resulting residue partitioned between ethyl acetate (100 ml) and citric acid solution (0.5M, 75 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (4×25 ml)
  6. washthe combined organic extracts were washed with water (50 ml) and brine (75 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by flash chromatography on silica gel
  11. washeluting with ethyl acetate: cyclohexane (1:1)

Sources & evidence

ORD record
ord-cf1275365dd140acb940194159b919a3
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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